Okay... Who is the luckiest guy in the world?

[Touch'EmAll]

Joe Montana has the world pretty much in his pocket. Great wife, great career, great post-career, great life!

[novakjr]

I'm gonna go out on a limb and say Justin Timberlake. Every time I turn around he's bangin' a new super hot chick...For FREE, I might add. That's really my only knock on Hef. He's technically not paying for them, but the chicks aren't really lining up for him, as much as they are the "idea of him", or what he can do for them.

Anyways, JT's roster includes Brittney Spears, Fergie, Jenna Dewan, Alyssa Milano, Cameron Diaz, Scarlett Johannson, and currently Jessica Biel. Plus rumored relationships/hookups with Rihanna, Ciara, Madonna, and Janet Jackson. Not to mention, the quality of groupies he's probably had available to him at live performances.

I'm not a fan or anything, but DAMN, dude's gotten ahold of some top-tier caliber women.

[glynparson]

Leon got it it's Heff.

[dstraate]

Originally Posted by 100backstroke

Joe Montana has the world pretty much in his pocket. Great wife, great career, great post-career, great life!

I dunno, anyone who has to resort to selling ShapeUps can't be all that lucky.

My vote goes to Matt McConaughey. Heff works way to hard.

[SteakNchop]

How about Derek Jeter?